Acquiring & Operating Value-Add Investment Properties with Tyler Chesser – EP 211

The Fastest Way To Build A Six Or Even… Seven Figure Real Estate EMPIRE! 

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Today, I’m talking with award-winning real estate entrepreneur and personal growth thought leader, Tyler Chesser. 

Tyler is the Co-Founder and Managing Partner of CF Capital — a national real estate investment firm that focuses on acquiring and operating multifamily assets. His team leverages its expertise in acquisitions and management to provide investors with superior risk-adjusted returns, while placing a premium on preserving capital.

Tyler has extensive experience as a multifamily real estate investor, consultant, business coach, and was previously a commercial real estate broker. 

He’s also the creator and host of the Elevate podcast, where he dissects the elements of exceptional achievement and lifestyle design with a focus on personal growth and real estate investing. 

In our conversation, Tyler takes us through his real estate journey, from residential broker, to commercial broker, to limited partner, to finally becoming an owner/operator. 

Listen in as we fully dissect the 247 unit deal that Tyler’s firm is buying in the Indiana market. He outlines their process for sourcing the deal, funding the deal, making value-add improvements, and mitigating risk to ensure all general and limited partners win big. 

One of my favorite parts of the conversation was getting Tyler’s take on the most important factors for evaluating whether a real estate deal is good OR bad. Some great insights from someone who’s seen it all! 

Tyler also shares his best advice for those starting out and explains why building relationships was the foundation for his success. 

Whether you’re looking for a great team to passively invest with OR you just want to learn more about how to structure your next deal, you won’t want to miss my conversation with Tyler Chesser!

Key Takeaways with Tyler Chesser

  • How Tyler’s syndication fund is structured and provides investors with superior risk-adjusted returns.

  • Dissecting a 247 unit deal – finding it, raising the money, beating out competition, value-add improvements, rent bumps, property management, and more! 

  • How to mitigate risk and build fail-safes into your multifamily deals so they can win in the long-term — regardless of what happens with inflation or cap rates. 

  • The downside to running a private equity fund.

  • Hear how Tyler got his start in real estate and went from residential broker, to commercial broker, to limited partner, to being co-founder/partner of CF Capital.

  • The characteristics that make for a good multifamily deal. 

  • Red flags to look out for when evaluating a deal.

  • Slow down and take some extra time to invest in relationships.

  • Why the most growth always comes on the other side of your biggest challenge — and why Tyler’s grandfather was his biggest role model

Tyler Chesser Tweetables

“Hope is never a strategy. Reality, research and actual performance is your strategy.” – Tyler Chesser

“One of the things that I've recognized is so important in this business, it's almost the central theme that's more important than anything, is relationships.” – Tyler Chesser


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Josh Cantwell: Hey, there. Welcome back to Accelerated Real Estate Investor with Josh Cantwell. So, excited that you continue to join me every week wherever you get your podcast and listen to our episodes, whether it’s having a guest star like the guest I’m about to have, Tyler Chesser, or whether it’s a solo cast. Just want to say thanks. Don’t forget to hit the subscribe button so you never miss another episode. And also, don’t forget to catch the episodes as well on YouTube so you can see the video version of all of these episodes. As mentioned, my guest today is a successful multifamily real estate investor named Tyler Chesser. Tyler is an active and passive multifamily real estate investor, and he has witnessed firsthand the successes and failures of building a real estate portfolio. Tyler is also the host of a popular top 200 global business podcast called Elevate, where he sits down with top real estate investors, entrepreneurs, and other recognized leaders and high performers and how they’ve been able to create an uncommon life. Tyler’s mission is to bring the message and the practical tactics to millions of people that a life without limits is not only possible but inevitable through the combination of successful multifamily commercial real estate investing and a defiant commitment to personal growth. 


In this episode, I ask Tyler, number one, what makes a good real estate investment? And number two, what makes a bad real estate investment? You will hear Tyler’s take on that. In addition, you’ll hear a very recent case study of a 248-unit that Tyler is buying in the Indiana market. And finally, number three, you’re going to hear about Tyler’s transition from the corporate world to being a residential real estate broker, to converting to a commercial real estate broker, to investing as a limited partner, to finally and where he is today, successfully being an owner, operator, and sponsor of multifamily apartment real estate investments all over the Southeast United States. Tyler is the co-founder of CF Capital and the host of the Elevate Podcast. I think you’re going to love this next episode of Accelerated Real Estate Investor with me, Josh Cantwell and Tyler Chesser. Here we go. 




Josh Cantwell: So, Tyler, look, I’ve been looking forward to having this episode and have you on the show for a long time. Thank you so much for joining me on Accelerated Real Estate Investor.


Tyler Chesser:  Josh, it’s my pleasure, my friend. We’re having a great day together already, so let’s keep it going. What do you say? 


Josh Cantwell: Heck, yeah. We just got done recording for your show. I’m excited to have you on talk more about you this time, so I’d love to know what specifically you’re working on, like today, like even this afternoon or next week that you’re excited about. What is a deal that maybe you’re working on or a raise or an event, something that you’re kind of juiced up about and passionate for? 


Tyler Chesser: Super excited because we’re buying a 247-unit deal right now in Evansville, Indiana, the third-largest city in Indiana. It’s a value-add C-plus kind of asset in a B-market. It’s like one of those unique deals that it almost seems you can’t find in this marketplace so we feel blessed and grateful to have this opportunity. We’re raising a little over $3 million for the deal and we’re about 75% of the way there and we just launched it a little over a week ago. So, we’re really, really excited about that. And we’re pumped, man, to get our arms around this opportunity and to lift this community. So, that’s probably what I’m most excited about right now. 


Josh Cantwell: Awesome. Fantastic steps. Let’s peel back the onion on that deal and also on kind of the way that you and your company make money. You run a private equity fund, you are investing in the Southeast, primarily. This deals a little bit more in the Rust Belt. Help us understand maybe a little bit about this deal or other deals that you do. What’s your typical structure look like? GP/LP, help us understand what the lift might look like or the CapEx and what the stabilized values are. Help us understand what your structure is. 


Tyler Chesser: Absolutely. Thank you for asking me and thanks for giving me the platform. Our company is called CF Capital and we’re headquartered in Louisville, Kentucky, and we really invest within about a three to four-hour radius of where we’re located. And we are continuing to expand further southeast as we continue to grow. But of course, Indiana is not too far away from where we’re located, in particular, but in terms of our overall strategy and how we really kind of split up GP/LP splits and all those kind of things, and actually I’ll back up first because what we do is we focus on value-add assets in this region and typically 150 to 300 units typically so that we can on-site staff and we can support a staff and we can put a great team on the field. But in terms of how we really approach deals, I mean, we typically look at deals and we’ll say, “All right. Well, we’re going to pay a preferred return, whether it’s 7% or 8%, whatever that may look like to investors.” And by the way, we invest in every single one of our deals so we always participate in the ballpark of 10% of our equity and we provide a preferred return. And above that preferred return, typically, we’re at a 70-30 split, 70% to limited partners, 30% to general partners, up to perhaps a particular IRR so that we’re incentivized to outperform if we like as an example, if we had a 15% IRR, we’ll typically go to a 50-50. 


And our goal is really always to exceed expectations for our investors, for the people that we work with, and so that’s how we make money. And of course, there are fees involved in the deals but we never like to overburden our deals to any degree. But we need to make sure that our team is supported and that our technology and our deal sourcing and all of these things are supported. And so, that’s how we approached the deal but happy to go in-depth on any of that, Josh. 


Josh Cantwell: Yeah. Fantastic. So, this deal in Indiana, right, like I love to talk about like very recent stuff that’s going on because it helps our audience and me get a sense of what you’re seeing in the marketplace. 


Tyler Chesser: Sure. 


Josh Cantwell: So, how was a deal like that found? Why Indiana? Like, what are you seeing in that particular market that you really like? What did you see about that deal that you liked? What was the upside opportunity there between the deal itself and the market? 


Tyler Chesser: So, we sourced the deal from a relationship with the broker that we have. Actually, this broker is based in Nashville, Tennessee, and they have a tremendous activity in Nashville, as well as Kentucky and Indiana, as well as other further states in the southeast. And we’ve actually established a great relationship with them in Tennessee. And believe it or not, they have a great relationship with an owner in Evansville, Indiana. And actually, it was interesting because they don’t typically operate in this market. Now, they do have another team within their office that operates in this market but our relationship with this broker put us in the forefront of this opportunity and we were able to strike at a time where the seller said, “You know what, it’s time to make this happen.” They were marketing the asset, I will tell you that, but we were able to preempt the marketing campaign to a very high degree and we were able to secure this deal before a tremendous amount of competition really kind of honed in on this. And so, our thought process behind more of this tertiary type of market is right now in the current marketplace, as you know, Josh. I mean, these assets are compressed to a very high degree, especially in the markets that are on the front page of your Financial Times or what have you, right? 


Josh Cantwell: Right. 


Tyler Chesser: So, we’re trying to look where the masses are not looking. We’re also trying to serve a clientele that maybe is not being served to the highest degree. And we’re also trying to mitigate our risk and be as conservative as possible and understand that, of course, there are risks in this type of strategy that may not be present in more of your primary or secondary markets. And so, we take that all into account but that’s how we were able to secure the deal. And in general, that’s how we’re looking at it from a very conservative perspective. But in terms of this particular deal, what it is, it’s so interesting because you and I had a conversation right before this on my podcast. You were talking about a lot of the markets in the Midwest have been virtually untouched or some of the assets in these markets have been untouched in comparison to a lot of the southeast markets. This asset is right in that sort of framework. And it was built in 1975. The units have not been upgraded cosmetically literally since construction. You know, the amenities across the property really need a lift and so we’re going to go in there and lift the entire asset up from all of those vantage points. So, happy to go into detail but let me know where you want to go with that, Josh. 


Josh Cantwell: Yeah, absolutely. So, Midwest value-add, we talked about what is your definition because something like value-add, we’re going to bump the rents 10%. We’re going to add some lipstick. Like my idea of value-add is 5,000 to 7,000, even 10,000 a unit and a big rent bump when we’re done of sometimes $150 to $300. Help us understand what your thoughts are on value-add and what you saw in that market versus some of the stuff that you’re seeing in the Southeast right now. 


Tyler Chesser: Yeah, absolutely. So, what we’re doing here is we’re putting in $4,000 a unit and that comes to LVP flooring, countertops, some appliances. I mean, that’s basically it. I mean, fixtures, hardware, just the simple stuff. And really, we’re actually projecting a very conservative $70 rent bump. And I think we can outpace that. I think we can outperform our expectations on CapEx but, again, we’re trying to be as conservative as possible. I think it’s possible that we spend somewhere in the 3,000 to 3,500 a unit range and I think it’s possible that we bump rents $100 to $125 a month. But of course, from our projection standpoint in where we’re at, can we live with that projection? Absolutely. And so, we think it’s really, really conservative. When we look at the rent stack and where we still land, we’re actually still on much of the lower end of that spectrum and I think we’ll have a great final product there. But we also like we were talking about earlier, Josh, we’ve got a tennis court on site here. We’re actually going to be converting into a dog park and a dog washing station right next door because most of the tenants have dogs, right? You know, what’s actually really unique about this property is that the majority, actually, all of these units are one bedrooms and studios. And so, there’s not a lot of children. There’s not a lot of families on-site. So, typically you’d look at this and say, well, we definitely need a new playground and all these things but we’re not doing that. 


We have folks who are single or maybe it’s couples or maybe it’s older people but most of these people have dogs. And so, we’re trying to create a more of a sense of community. And there’s also an indoor pool on-site here. So, looking to upgrade the furniture and upgrade that experience and also put like a grilling station outside so that people can have an experience where they meet each other and have a good time. But it’s just an asset that there’s so much low-hanging fruit across the board, in addition to the fact that we can put professional property management on-site, where right now our seller has been managing within his company. And there’s nothing wrong with that, of course, but we’ve got a third-party property management company that we believe is best-in-market and we can go in there and really put an amazing team on the field and we think that there are many operational inefficiencies that can really be shored up very quickly. So, that’s the way that we look at it. But, of course, I mean if you’re buying a similar deal and you call it a Nashville, Tennessee, or Charlotte, North Carolina, or Raleigh, I mean, you’ve got to see a much more significant rent bump and perhaps your renovation costs are going to be higher, no doubt about it. And so, there’s just a lot more competition so there’s just more margin in this type of deal, if that makes sense. But yeah, go ahead. 


Josh Cantwell: Love it. Love it. So, when you’re looking at deals like this in today’s market and the market feels like cap rates are low, I don’t know if they can go any lower. You know, you feel like the government’s doing a lot of printing money. What are some of the things that you’re thinking that’s going to happen with the market? What kind of value you’re adding in or protections you’re putting into your underwrites to make sure that over the next one to three to five years, these are winning deals? They’re not just buying them for today or investing for the long haul. So, help me understand some of the risks that you’re incorporating in your underwrites, things that you’re saying, “Well, we’ve got to really make sure that we include this,” whereas maybe three or four years ago, the market was getting hotter and hotter and hotter and we didn’t think it would even get to this point but now we’re there. There are still deals happening but there’s some risk that we have to account for. What are some of the things that go into your underwrites that you’re saying, “We’ve really got to make sure that this is included.” 


Tyler Chesser: So, one of the things that I’ll say is I believe that the ultimate sign of intelligence is balancing two opposing viewpoints and considering both in making a decision based on what you feel is most appropriate. And I think that’s really important in real estate investing and especially in multifamily real estate investing in this current climate because we have, in my opinion, winds flying from every direction, right? You’ve got money being printed to a higher degree than we’ve ever seen in human history. You’ve got lockdowns in certain markets. You’ve got open markets. You’ve got companies that are shutting down. You’ve got people that are receiving stimulus. You’ve got a huge demand for assets because of the expectation for inflation. And I wouldn’t anticipate that to really slow down but, of course, we’ve got to consider all circumstances. So, one of the things that my mind goes to when you ask me that question is we think about cap rates, right? If we’re thinking about inflation, if inflation is going to be felt in assets, perhaps what that means is that our cap rates are going to continue to compress. Now, one thing that I’ll say is we can never really guarantee what a future market is going to be. So, that’s one of the hardest things I believe that we have to do in our business is determine an exit cap rate. 


So, one of the things that we always try to do is increase our exit cap rate. So, if we’re buying a deal at a 6 cap, we like to increase our cap rate by 10 to 20 basis points on an annual basis. If we’re going to hold the deal for five years, that’s what our increase will be. Now, every deal is unique. Now, if we’re buying a deal at a 7 cap, as an example in the current market, it’s probably unlikely that five years later we’re going to be exiting at an 8.5 cap just based on everything that’s happening. So, every deal is unique. Every deal is its own business plan and its own set of circumstances. And so, one of the things that we’re doing right now that we’ve seen has allowed us to be more competitive is to source more bridge debt because of proceeds and obviously terms in general. And so, what we’ve done there is we’re buying interest rate caps because, of course, this is a unique environment. I cannot and I can’t really foresee an environment where interest rates significantly go up just based on the fact that our entire system is really propped up on so much leverage. Now, is it possible? Of course. And so, we’ve always got to be willing to adapt and take on those circumstances but those are just a few considerations that we have in today’s environment but I’m curious if there’s any further directions that you like to go with that. 


Josh Cantwell: Yeah. Absolutely. No, that’s great. I think building in some failsafes over the next couple of years for inflation to go up, cap rates to possibly go down, or depending on again what people’s appetites are. You just got to really stress the numbers, make sure that you can exit, whether it’s a refi or a sale at not the best numbers. I like to tell our investors, “We’d like to get to stabilization, let’s say, at four years,” when I know my real goal for stabilization is two. Or our goal is to sell or refi for five years when I’m really thinking with our internal team is at three. And if the deal still works at five but our goal is three, then awesome. Let’s make that happen. Tyler, I’m curious to see you invest through a fund. You guys have a private equity fund. You guys also have one-off deals. You guys do different structures. What’s your thoughts? You’ve done deals both ways. Through a fund, without a fund, one-off? What is your favorite way to do those deals? Why do you have a fund? And then what are some of the different benefits to a fund structure that you’ve seen versus a one-off structure? What is that structure for you and your company? 


Tyler Chesser: Yeah. And so, I’ll actually just correct you because we just do one-offs so we raise individual deals. And so, we’re at in the current environment. We feel that is the most appropriate just because of how challenging and how competitive the environment is. We don’t want to be put in a position. At least this is where we are personally in the stage of our company right now. We don’t feel that it’s appropriate to have the funds aside to feel like we have to deploy that within a certain amount of time. And so, with our investor community, we do raise on an individual deal-by-deal basis. And so, I think that there will be a point in time where it makes sense for us to deploy a fund in terms of that capacity but that’s not where we’re at right now. 


Josh Cantwell: Got it. Yeah, makes a lot of sense. I was actually hoping you’d say that because we ran a private equity fund. It definitely feels like you’re constantly in a rat race or on the hamster wheel recruiting money and finding deals to match versus now it’s for us to raising capital but it’s really getting soft commitments. It’s talking to investors. Hey, if we find the next deal, how liquid are you? How much money do you have? If we do raise for this, can you commit to it? Then you’re out finding that deal. And then when you find the deal, you do a webinar, which is what we do, and people make the commitment. It’s much easier to handle that way. And I hate to have what we call cash drag sitting there with cash and interest rates that we have to pay with no deal flow to do with it. It’s great stuff. So, let’s back up for a little bit and talk a little bit more about your start. Multifamily, cash flow, investing is your passion today. Has it always been your passion and how did you get into it? 


Tyler Chesser: No. I mean, I didn’t know anything about this growing up. I mean, I grew up middle class, similar to you, Josh. And when I got out of college, I started in the corporate world because for me, I always thought that, “Hey, that was the ultimate level of success is climbing the corporate ladder. And maybe someday I’ll be in the C-suite or something like that. Who knows?” It wasn’t even really a clear direction that I knew I was going down. But ultimately, I learned that the politics of the corporate world were not something that I wanted to experience for the rest of my life and that was really early on in my career. And so, thankfully, I went through a challenge and it honestly took me probably a couple of years to really manifest in those feelings of a little bit of frustration and maybe feeling like I was tolerating my life. And so, ultimately what I decided to do was I decided to go and get my real estate license because I actually went to a seminar and I took a little personality assessment and they said, “Hey, you would make six figures if you were a real estate agent.” I’m like, “Man, six figures sounds amazing. I’m like in this corporate job where I’m asking for raises all the time and they’re barely giving me 2.5% or 3%.” 


And so, I ended up getting my real estate license and I went out and I immediately started selling homes and I learned very, very quickly that selling residential real estate was definitely not going to be for me in terms of how emotional it was and all the different dynamics of selling residential real estate. So, I pivoted very quickly into selling commercial real estate and income-producing real estate. First of all, I had no idea that real estate produced income, which is as silly as it can even sound, even with the conversation we’re having today. And I learned about the fact that real estate can produce income but it can also produce massive wealth. And 95% plus of the world’s millionaires or multimillionaires have a significant portion of their wealth in real estate or have made a significant portion of their wealth in real estate. And of course, you learn from great people like Robert Kiyosaki that this is how rich people think and it isn’t about, hey, beating on my chest and saying, “I’m rich,” or anything like that but it’s about developing a lifestyle. And so, as I started to sell income-producing real estate whether it was retail, office, industrial or multifamily, I started to learn how investors think. And I actually built a niche in multifamily real estate brokerage and was selling a ton of real estate and actually became known as the apartment guy. And as I was selling, I started to build relationships and learn more about what makes a good deal, a good deal, and what makes a bad deal, bad deal. And how did the best of the best negotiate these deals and operate and execute on a business plan? And so, I decided, “Hey, this sounds amazing for me as well. Let me try this, too.” 


And so, I started to invest my own commissions into multifamily deals. Like the first deal I ever did was an 8 plex and I learned sort of the hard way that it’s not as easy as it looks and there’s a lot of considerations that maybe we don’t consider when reading about it in a book or selling it as a real estate agent or a real estate broker. And so, that’s really been my trajectory. As I’ve continued to grow, I started investing my own money on smaller deals, medium-sized deals, larger deals, and I started investing as a limited partner in other people’s syndication so that I could learn more about scale and more about those economies of scale and how that really manifests. So, that’s been my trajectory. And of course, now we do these deals ourselves and we bring in private capital as a function of that. So, it’s become a passion of mine because of the lifestyle that it can create and the options that it creates. In my opinion, if you only have one option, then you have none. And what real estate and multifamily real estate allows you to do, not only from actually the direct mechanisms of the property itself in terms of so many different units and so many different options in terms of how we can add value and how we can mitigate risk but also on the back end in terms of the different flows of income and the upside and the tax benefits and all these different things. So, that’s why I love multifamily real estate. 


Josh Cantwell: Nice. Love it. Now, you said something I want to peel back the onion on a little. You said you learned what made a good deal, a good deal, and you learned what made a bad deal, a bad deal. So, let me just ask you, in your opinion today, what are some characteristics that make a good multifamily deal a good deal? 


Tyler Chesser: I love that. I would say you’ve got to have some margin for error because a pro forma is just that. It’s a pro forma, right? It never completely lines up in the real world to be that way. So, like one thing we were talking about earlier is exit cap rates. I was looking at a colleague’s deal and they had a sensitivity analysis on what they were looking to exit their deal in five years or whatever. And it was like between a 3.5 cap and a 4.25 cap and I’m like, “All right. I get it. It’s in a great market and all this stuff,” but for me, that’s a little bit risky. And if you’re hitting a mediocre internal rate of return projection on those types of assumptions, to me, that’s a very risky deal. It’s a very challenging deal. So, for me, I like to see, well, what’s the in-place cash flow, what’s the historical performance of this asset, and what can we reasonably project into the future based on that? Not something that we’re hoping and wishing because hope is never a strategy. Reality and research and actual performance is your strategy. So, how can we do that? So, for me, it’s always about doing great due diligence and so understanding what’s the reality of this property and what can we project moving forward. So, I mean, I could go on for hours and hours and hours about what I think is a good deal and what’s a bad deal but I always try to be conservative. And if I don’t feel like the conservative estimates are what’s within the realm of possibilities for this asset, then we need to move on. Because you know what, you can lose so much. It’s almost like your reputation, right? It takes 20 years to build a reputation and 20 seconds to destroy it. It’s the same in investing. 


Josh Cantwell: Love it, love it, love it. I do need to ask you, what are some things that pop out when you look at a deal and underwrite a deal? That making a bad deal where you’re like, “Immediately I see this, this and that. I’m out. I’m a hard no. I’m not going to even offer. I’m not going to go look at it. I’m not going to spend any more time underwriting it. It’s just a bad deal.” Are there anything red flags that pop out of the deal that you can immediately say, “Hey, if you’re in the audience and you’re listening to this and you see this or that, it’s probably not a deal.”? 


Tyler Chesser: I would say, I mean, the first thing that comes to mind is expense ratio. I mean, for the most part, unless it’s a new construction deal, you’re really going to be looking at 45% to 50% expense ratio. And so, if you’re projecting a market cap rate acquisition at a 40% or less expense ratio, that’s probably a red flag that it’s going to be unrealistic for you to operate that asset in that capacity moving forward. So, if that’s the expectation, if that’s what the competition is basing their assumptions on, it’s probably best to let that go to the competitor. Does that make sense, Josh? 


Josh Cantwell: Absolutely. Absolutely. I agree. You know, anything under that really 45% is going to be tough to really meet unless it’s a really small deal, an 8-unit, a 10-unit, a 12-unit, something like that. And in that scenario, might be able to do a 42% or a 44% expense ratio. Well, any larger asset that generally 47.5%, 48% to 51%, 52% is probably where it’s going to land. I love to see deals that we’re buying where the current operator is at like a 60% cap rate or 65% cap rate. I mean, not a cap rate but an expense ratio because you know that there’s operational inefficiencies there that you can immediately fix. I love to see that stuff. Tyler, so I want to ask you, now that you’ve had success in multifamily, being a broker, being an owner-operator, raising millions of dollars of private money, what kind of advice would you give your younger former self? Like, what are some things that you did along the way that maybe you wish you had done differently? Or what are some things or some deals along the way that you didn’t do that you wish you did? What advice would you give your younger former self or what advice would you give our audience that you’ve learned along your journey? 


Tyler Chesser: It would be take the extra time to invest in relationships because I noticed as I was coming up in the business, and I still notice this at times, I have to remind myself to slow down a bit and really focus on that relationship because I’ve found myself to be ambitious and driven for my own goals and focused and growth-oriented and all these things. But sometimes you almost have to slow down to speed up. And one of the experiences that I learned early in my career, I actually, as a broker, I was closing a deal and I was actually the dual broker on the deal. And at the closing table, I’m sitting there with both parties and one of the parties is asking the other about his son, who had recently left for the military and he was asking him all these detailed questions and I’m like, “Man, first of all, I didn’t even know he had a son.” Second of all, I didn’t have any clue he was going to the military. And so, one of the things that I’ve recognized is so important in this business, it’s almost the central theme that’s more important than anything, is relationships. So, for me, if I were to give advice to my younger self, it would be slow down and ask more questions and focus on this other person without any expectation for anything in return. It’s just focus a little bit more on people. 


Josh Cantwell: Yeah. Love it. So, listen, Tyler, as we kind of round third here, head for home, the last piece of this interview, this podcast is what we call the final five questions. Jump in with as fast of an answer as you can think of to help our audience get some more perspective about you and how you look at life and how you look at deals. So, question number one of the final five is what’s your favorite way to find deals? 


Tyler Chesser: Through relationships, whether it’s through brokers or direct to seller. I mean, I have a special place in my heart for brokers. That’s my previous life and I know how hard brokers work. I know how much goes into sourcing those deals in those relationships. So, I do always like to prefer to really invest in those relationships. So, I would say my favorite way is going through brokers who have my best interests at heart that can really deliver results and add value to the deal as well. 


Josh Cantwell: Nice. Question number two, your favorite way to find money or joint venture partners to fill up your capital stack? 


Tyler Chesser: People that I love to hang out with, people that make me laugh, people that are sharp, people that are driven, but they’re also ready to have a good time. And our investor community is that way and the people that we work with on a joint venture, strategic partnership capacity as well. It’s people who are the best in the business but they also don’t take themselves too seriously. So, that’s my favorite way to access capital. 


Josh Cantwell: Nice. Next question. What’s your favorite place to think? Your favorite place to go to decompress? 


Tyler Chesser: I would say it’s probably so I’ve got a nine-year-old German shepherd. His name is Bruno and we go on walks every single day. And I’ll tell you what, man, I have some of the greatest thoughts when I’m on walks with him. A lot of times I’ll listen to the podcast but sometimes I’m not. And actually, more recently, most of the time that I have not been listening just because I’ve been giving myself a little bit more space. And it’s pretty amazing. In fact, actually, my secondary answer to this question would be reading because the other day I was reading a book and I had been working on a problem and thinking about this challenge that I’ve been having for weeks and weeks and weeks. And all of a sudden, it just came to me out of left field and so, it’s so interesting. I just gave myself space to learn. And one word that I was reading in that book gave me the answer to this challenge that I’ve been banging my head against the wall. So, those are just a couple of examples. 


Josh Cantwell: Love it. Love it. Favorite book or favorite piece of advice that you’ve ever been given? 


Tyler Chesser: Oh, my gosh. I’m a huge reader. I read all the time. In fact, typically I’ll read one book a week and that’s just because it’s my habit. I mean, I read every single morning for at least an hour or so. So, it’s a tough question for me to say, what’s my favorite book. I mean, one of my favorite, most recent books has been The Art of Impossible, and that’s by Steven Kotler. I was blessed and grateful to have him on Elevate podcast but that is a phenomenal book for anybody who’s looking to do things that most people consider impossible in their life. Or maybe they have been considered impossible in terms of what societal expectations are. That book is phenomenal and it really gets into the nitty-gritty so I highly recommend that one. 


Josh Cantwell: Nice. And last but not least, who’s the favorite mentor that you have ever had or the person that’s probably had the biggest impact on your life? 


Tyler Chesser: I’ll tell you what. I mean, I’ve had a lot of mentors, and one of the things that I’m really passionate about is that success leaves clues. But I’m actually going to give you an answer to this that maybe left field and doesn’t really fit exactly what I just said because one of the biggest mentors or role models in my life was my grandfather. He was a dairy farmer and he actually learned when he was 40 years old that he was diagnosed with multiple sclerosis and he actually woke up one day and could not walk. And so, you think about a guy who used his body to provide for his family for his entire life and then all of a sudden was not able to walk or do what he did. And he had a dream to be a successful entrepreneur as a farmer, and he was, but he pivoted his life. And when he ultimately passed away, probably 35 years later, he had, I mean, I tell you what, he had thousands and thousands of people at his funeral and the reason why is because he was still able to impact people with his identity totally pivoting. And so, to me, I think that’s an extremely powerful example, that when life throws challenges at us, that that may be our greatest gift and it may be our greatest opportunity to impact someone else. So, to me, that is probably the best role model that I’ve ever experienced in my life. 


Josh Cantwell: Yeah. The most growth typically comes on the other side of the biggest challenge, right? Fantastic stuff. Tyler, listen, our audience, I’m sure, is going to want to connect with you, learn more about your business, your philosophies, your podcast. Where can they get more information about you?


Tyler Chesser: Yeah. I mean if your listeners like podcasts, obviously, they can go check out Elevate Podcast. It’s available on every single podcast platform that’s out there. It’s all about mindset, mind expansion, and personal growth for high-performing real estate investors. So, you can also check that out at or if you want to learn more about what we do at CF Capital, just go to And of course, I’m on all the social media platforms as well, so I’d love to connect. 


Josh Cantwell: Awesome stuff. Tyler, listen, thank you so much for joining me today on Accelerated Real Estate Investor. I love this interview. 


Tyler Chesser: Thank you so much, Josh. It was a pleasure, my friend. 




Josh Cantwell: Well, hey, guys. Listen, I hope you really enjoyed that episode of Accelerated Real Estate Investor with me and Tyler Chesser. I love that episode specifically where Tyler talked about what makes a good deal and what makes a bad deal, and also specifically about his 248-unit case study. I also love to see his transition from the corporate world to being a resi broker, to being a commercial broker, to being a limited partner, and then to being an owner-operator very much like me, an organic sort of growth or organic change where the next step just happened by putting one foot in front of the other. If you enjoyed that episode, don’t forget to subscribe. Hit the subscribe button so that you never miss another episode of Accelerated Real Estate Investor. Also, share this episode all over social media and help us build this Amazing Accelerated Real Estate Investor community. Don’t forget to leave us a five-star review and a rating wherever you get your podcasts. And also, finally, don’t forget to join our private Facebook group on Facebook. It’s absolutely free to join. Go to Facebook and look up Accelerated Real Estate Investor. Join the group now for free so we can communicate. Talk directly with me. I can answer your questions and we can network and mastermind together. Thank you so much for joining me again on Accelerated Real Estate Investor. We’ll talk to you next time. Take care.


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